Some things, I'm glad I failed slow at

Quite naturally, we all want to avoid making mistakes. Not only is there a sense of time wasted doing the wrong thing, but the emotional expenditure of making mistakes takes a huge toll, and can even permanently injure. Still, we also know that failure presents pivotal, formative moments in life. Failing at certain things has made me more self-aware. And it has made me more empathetic too.

The "fail fast" school of thought tries to capture the best of both worlds: Get all the learning benefits of failure but in a get in-and-out-fast way, with as little injury and time wasted as possible. I'm a fan of failing fast. And it works especially well if you're talking about projects and experiments that can be parsed and measured. But life isn't always so neat. And measures of success are often unclear and/or subject to change over time.

There are some things that I believe I needed to fail slowly and painfully at; experiences that I would not have learned from unless I had endured them beyond the fail-fast timeframe. These failures continue to teach me now, as they change hue and become key moments in my past; fail fast experiments simply don't resonate for as long.

(1) Living in the wrong neighbourhood / city

This is a hard one for me to talk about because, although I've been lonely and lost in so many places, I've always ended up feeling the experience was rich. I guess this may be the lesson: I can't really move somewhere and think that my happiness is reducible to a checklist. Ultimately, it boils down to something ineffable between me and the place I'm in.

The beautiful thing about living in different places is that each one is a different kind of incomparable relationship. The hard thing about living in places is that, unlike a relationship with a person, a city is ultimately indifferent to you. Learning that much of what I'm feeling is defined by me alone, is something that hits home only with time, when connections inevitably develop and I realize the option to build is always there, even if the desire is not.

2. Loving the wrong person

To be clear, I wouldn't wish anybody into a bad/abusive relationship. That's not what I mean by wrong person.

I mean loving the wrong person where there's no real blame on either side. The feeling of loving somebody who isn't "the one" is one of the sweetest kinds of love I've experienced. Understanding that I was wrong for them, and they were wrong for me, and yet we could share something special and care deeply for each other.

Such relationships taught me that love isn't all there is to a relationship. They taught me that finite, impossible things are special and worth experiencing too. And, most importantly, they taught me that just because there's pain, it doesn't always mean there's fault.

3. Failing at a really important friendship

Losing a best friend is such a devastating thing that I'm always astonished we don't have better language to talk about it. We often we feel we are more ourselves and more forgiving of friends, that we ask less and share more. So, when that ends, it's hard to not feel like you have truly fucked up something important.

There's also stigma associated with failing at a friendship. I don't talk about ex-friends as openly as I do ex-lovers; it never stops feeling like a failure and there is no pithy wisdom to take from it. But friendships can be "off" relationships too: They can lack balance and erode. And sometimes the connection just disappears and you find yourself more troubled than comforted by this person who knows you so well.

Failing at friendship is one of those failures that never feels resolved for me. But I also think a world of neat conclusions is a lie. Failed friendships have made me think differently about my friends, both new and old. Friendship is not just the emotional side-dish to romance, as it's so often portrayed. In fact, for me, friends are most important relationships of my life, and the failed ones are as much a part of that as the ones that survive.

4. Working in a place that's all wrong

I covered this a lot in this post. But there's one thing to getting into a situation like I did and quickly seeing it's all wrong. There's another to getting into the wrong role and persevering and even building some success at it. This was media and journalism for me.

I stayed in media for twelve years not because it was right for me but because I was still learning from it. There's a lot of emphasis on doing what's right for you and not compromising on happiness, but it's usually framed with a great deal of immediacy. Media was wrong for me as an industry, but the things I learned there and the work I did were formative and the foundation of this stage of my career. I don't think of my time in media as time wasted, the opposite in fact. You can simultaneously fail slowly in one sense, all the while succeeding in another.

5. Failing at finances

Finances are important. I don't at all self-identify themselves as "finance" person; my own default state is a blend of happy-go-lucky and daydreaming. But, I live and lust and engage in a world where money matters. And though it doesn't matter to me as a thing-in-itself, it does matter to me in a way that impact my lifestyle, which I do very much care about.

Living, as I do, more or less deliberately disconnected from that reality, has meant that sometimes I get a bit of a scare over money. I've had some of those wide awake nights over money. My situation's not grave but it's not as healthy as it could be; it's like I'm always 10lbs overweight when it comes to my finances and ultimately I need to stop ignoring it. I'm trying to be savvier in this new job and to think about money without feeling that compromises who I am or turns me into a less spirited individual.

6. Failing to be a perfect child

We all disappoint our parents sometimes and I've done my fair share of that. But I suppose I'm thinking of a specific way of disappointing them: I mean when you forge your own path rather than following theirs. I mean the way in which you kill that voice in your head that measures yourself against your parents expectations and dreams for you.

To be fair, I don't know what my parents really think. There's so much projection that comes with those parental voices in your head. I think, for instance, that I could be disappointing because I emigrated, am a spinster, and childless, or a renter, or don't drive, and on and on... Still, learning to make choices contrary to those normative, parental voices has been a slog. It's only now, as I near 40, that my own voice has become the more established one. And I have to say, it's these contrary choices that I've made that have been the most defining for me.

7. Being a person you don't want to be

We are who we are. A leopard can't change her spots, and so forth... But we do also evolve and change, try on different personas and ways of being in the world. As a cuspy kind of introverted extrovert, I often feel like I have different personalities to choose from when I engage in the world. I can be tough and even brittle. I can be warm and funny. I can be aloof, shy, restrained. Because I am all those things.

But these mantles can also colour the world, for myself and those around me. There's a version of myself I can be that makes me wince when I'm alone. And I've lived and worked places that really brought that out in me. Understanding that I must actively decide to not be that person, that I must create the kind of life where I can be a version of myself that makes me feel like a kind person, is much more important to me now than so much else of what I'm doing every day.